When I told people I was selling the business, there was many that would not support the decision.
Bankers said hold. Friends said hold. My accountant ran numbers that said hold. The advice was unanimous: you are at the top of your run, the market is strong, multiples are high, ride this for two more years and triple your exit number.
I sold anyway. I sold at what I thought was roughly 80% of the absolute peak. That was the right call.
Here's what they couldn't see from outside the business.
The energy I had for it was running out. I had been at the wheel for over a decade. I knew the next phase of growth required a different version of me than I wanted to become. More travel. More middle management. More compliance. Less of the building I actually loved. The version of me that could ride the wheel for another two years was a version of me I didn't want to spend two years being.
That alone is enough reason to sell. But there were two other reasons that mattered just as much.
The first is that markets turn. The exact thing that made the multiples high in my category, namely consumer confidence, low rates, sector hype, was the same thing that could disappear in a single quarter. Sitting on a peak and waiting for a higher peak is how most founders watch their best exit window close behind them. By the time you realise the cycle has turned, the buyers have already moved on to the next sector and the multiples you were chasing have evaporated.
The second is that holding past the right moment is not free. There is an opportunity cost. The capital, the time, the energy you spend keeping the wheel turning is capital, time, and energy you can't spend on the next thing. Founders fixate on the exit number. They don't think enough about what they're forfeiting by staying.
There's a version of the story where I held for two more years and made an additional 50%. That version is real. It was possible. I also know what I built and what I started in the two years after I sold, and I would not trade it for an extra 50% on an exit I'd already mentally moved on from.
If you're staring down a real offer right now, here are four questions to sit with before you turn it down.
Are you still the right operator for the next phase? Businesses change as they grow. The CEO who built a company from zero to twenty million is often not the CEO who takes it from twenty to a hundred. If the next phase needs someone who flies 200 days a year, manages five layers of leadership, and spends most of their time in compliance and HR, ask yourself honestly whether that's the work you want to do for the next three years. If it isn't, you are already on borrowed time, and your performance will reflect it.
Is your category at a cycle peak? Look at comparable transactions in your sector over the last two years. If multiples are at historic highs and the macro environment is propping them up, holding for more is a market timing bet, not a business decision. Be honest about which one you're making. Market timing bets in your own business are still bets.
What would you actually do with the proceeds? If the answer is "I don't know yet", that's a real reason to keep working. Selling without a clear next thing leads founders into a bad place where they spend the money on things that don't matter and then quietly regret the exit. If the answer is "I have three things I'm already itching to start", that's a real reason to sell. The proceeds become fuel for the next phase, not a retirement fund you don't know what to do with.
If the offer disappeared tomorrow and never came back, would you regret turning it down? Sit with that one. The answer tells you everything. If a yes makes you genuinely uneasy, the offer is the right one. If you'd shrug, then walking away is fine.
The hardest part of selling at the right moment is that nobody around you will agree with you in real time. The validation comes later, sometimes years later, when the market shifts or the next chapter starts paying off. You have to make the call without the social proof, on your own read of your own business and your own life.
I sold and I built something else. The people who told me to hold are still riding the same wheel. Not all of them are happy about it.
If your business is past the idea stage and you're ready to scale with capital and mentorship, applications for Founder Finds Future open soon.